


Dear Fellow Traveler

by EaterofSouls428



Category: Supernatural
Genre: Alternate Universe - Pirate, Castiel Loves Dean Winchester, Castiel and Dean Winchester Need to Use Their Words, Castiel is Not Amused (Supernatural), Dean Winchester is Bad at Feelings, Dean Winchester is Not Heterosexual, M/M, Protective Dean Winchester, Sam Winchester Knows, Sam Winchester Needs a Hug, Sam Winchester Ships Castiel/Dean Winchester, Sam Winchester is Not Amused, Sam Winchester is So Done, Slow Burn
Language: English
Status: In-Progress
Published: 2020-10-29
Updated: 2020-12-16
Packaged: 2021-03-08 17:28:03
Rating: Mature
Warnings: Graphic Depictions Of Violence
Chapters: 3
Words: 5,967
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27260473
Author URL: https://archiveofourown.org/users/EaterofSouls428/pseuds/EaterofSouls428
Summary: The dread pirates Winchester and their crew of loathsome swashbucklers raid a village where Castiel, a weary traveler determined to see the world, happens to be staying. In an attempt to escape, Castiel accidentally has a run in with the captain of the Free Will, Dean Winchester himself. After rescuing Dean from certain death, Castiel joins the crew of the Free Will to avoid his own death.
Relationships: Castiel/Dean Winchester, Eileen Leahy/Sam Winchester
Kudos: 9





	1. Chapter 1

The scent of salty water filled Castiel's nostrils as he entered the large city of Illiac. Home to one of the largest amounts of people in one place. To carpenters, and fishermen, royal guards and sailors, as well as many others. Castiel was neither of those. He could not be bothered to settle in one place. He floated along like the salty mists of the sea. He had once called Illiac his home until he set out to travel as far and to everywhere he could.

He took himself, his skills, and a change of clothes when he left, never looking back. Until now. His mother, Naomi, was ill. The family had decided to be together to be with her in her final moments. None of the children had wanted to be there, but their father practically begged them to be there for him.

Castiel let out a groan. Wishing to be far from the place he had once called home. He hated it with every fiber of his being, but he'd do just about anything for his father.

He let out a sigh and decided he would head to the town square and try to barter for a meal with the merchants. On his way he noticed many things that Illiac had changed over the years. From the new stone streets to the erasure of the remnants of the war. As he walked past the docks he took note of every ship in the harbor. Noticing how they were all fishing boats. He remembered the time his older brother's had stolen one to escape their mother but crashed and sunk it. He remembered how angry their father was when he had to pay for it.

He reminisced in his childhood memories, especially the time Gabriel dared him to pierce his ear for 2 gold pieces. He almost missed being in Illiac, until he came to his senses. He kept walking towards the square until he was stopped by someone familiar.

"Castiel?" A familiar voice called to him. "Novak, is that ye? What're ye doing back 'ere in Illiac?"

"Ezekiel? Is that ye?" Castiel spun around and faced him. 

"nay, Gadreel. Ye ne'er could tell the diff'rence between the two o' us." Gadreel spoke with a smirk.

"Yer twins, ain't that always 'appenin' to ye?" Castiel said and sauntered over to Gadreel. 

"That may be true, Castiel, but ye still 'aven't answered me question." Gadreel reminded.

"Sorry, Naomi's fallen ill and the doctors think that she ain't livin' much longer." Castiel spoke through gritted teeth. "Me father's fallin' apart, y'know 'e loved 'er, she was the love of 'is life. The whole fam'ly's here fer 'im." 

"Yer whole fam'ly? All yer brothers an' sisters?" Gadreel choked. "ain't that dangerous? Ever since the last time ye all gather'd in one place..." 

"Yer tellin' me. Us siblin's can't stand each other and the only one that can stand our mother is Father, or Raphael but 'e's dead." "Castiel exasperated. 

"Raphael died?" Gadreel asked visibly disarrayed. "What 'appen'd ?" 

"The war, 'e fought vigorously an' died jus' the same." Castiel spoke. "Well, more gruesome. Blown to pieces, 'e was."

"Tha's a shame, Castiel." Gadreel shook his head. 

"What about you, Gadreel? Are ye keepin yerself out o' trouble?" Castiel asked.

"A royal guard." Gadreel spoke proudly. "I be protectin' the king 'imself now." 

"King Crowley 'imself?" Castiel spoke, dumbfounded that Gadreel had made such a name for himself.

"Nay, I be protectin' the streets o' Illiac fer now. Someday though, I be protectin the king." Gadreel spoke and turned toward the sun. "I better be goin' Castiel, got to get to work."

"I'll see ye, next time I be in Illiac." Castiel said and turned away from Gadreel. He started towards his Father's home and soon he was reminded of why he wanted to go to the square anyway. He looked towards the sun and saw that it was setting, he then decided it was too late and simply went to his father's home instead.

As he was just about to turn down the street where his father lived, a huge crowd of soldiers and royal guards came by dragging along a man, nearly trampling Castiel. He'd recognized the man they were dragging from a wanted poster that he saw when he first got into town. 

Samuel Winchester.

The dreaded First mate of the Free Will had been captured by the royal guard. As he saw the man being dragged away, Castiel felt a pit form in his belly. Something was going to happen to Illiac tonight. And he did not want to be there when it did.

As soon as he got to his father's house, Castiel had already wanted to leave. However, he drew all the strength he had in him and knocked on his father's door. As he waited he heard shuffling and two of his brother's arguing for the other to get the door. 

The door opened after their father stepped in. He opened the door and glared at Castiel for a few seconds before softening his face at Castiel's support during this time. 

"Castiel." His father spoke. 

"Father." Castiel said, waiting for his father's response.

"I am so glad you came, Castiel. Your mother is not well." His father sighed heavily.

"O' course, anythin' fer ye." Castiel said before realizing his mistake a second later.

"I'm sorry, do you go about your daily life speaking like that?" His father exclaimed in disgust. "You are an educated man, Castiel Novak. You should not be speaking like a common man." 

"I'm sorry, father. I meant it only in jest." Castiel hoped a statement like that would appease his father.

"I did not find the appeal. Now come, your mother will be elated that you are here." His father led him to their mother's bedroom where she sat, surrounded by the children she loathed. 

"Naomi, my dearest. Our youngest son has finally arrived." He spoke and sat next to his wife.

"Hello mother." Castiel spoke.

"Hello Castiel." She rasped. "Have you finally settled down with a wife yet?" 

Castiel grew upset but did his best to hide it. He had no interest in obtaining a wife, especially not settling down either. He simply said no and sat next to Gabriel. Soon after their father served dinner and the children sat with their father in the front room and ate. Naomi had no desire for food.

"Michael, Lucifer." Their father spoke while chewing on his strip of meat. "How well are the frontlines?"

"They are quite well in the north, father." Michael spoke blandly. 

"I cannot say the some for the South, the blasphemers, heretics and rebels are now joined in resistance by pirates." Lucifer smiled slightly, talking about heresy and rebellion with his father excited him. 

"That is quite troubling. Which of them have joined the resistance?" Their father shifted in his chair, quite intrigued.

"From those I've seen, Wayward Sisters, Fitzgerald and his crew, and of course the nastiest pirates of them all, the Winchester brothers." Lucifer said, waiting for his father's reaction. However he had no reaction. "The Winchesters are now leading this so called revolution."

"Those damned Winchesters." Their father spoke. 

"Quit talking about those Winchesters." Naomi yelled from her bedroom. "You should be trying to convince Castiel to continue his scholarship instead of being a disappointment!"

And with that, Castiel stood up and he began to leave. He'd had enough of his mother's torment. He took his uneaten food and set it back in the kitchen and bid farewell to his father, brothers and sisters. He opened the front door but before he could leave, his youngest sister Anna pointed out that he had forgotten to say goodbye to their mother.

"Yer right, Anna. Die swiftly and 'orribly Naomi. It'll be a blessin if I ne'er 'ave t' see yer ugly face again ye wench!" Castiel exclaimed and slammed the door behind him. 

Castiel ran his hand through his hair and sighed. Had he really told his own mother to die horribly? He almost wouldn't believe it, if he hadn't had said it himself. He quickly regained his composure however and decided to go to the Square to book a room at the Inn. As he was walking past the docks he noticed a ship docking, it was bigger than the rest and had more damage to it. He took note of how bad the repairs actually were. He looked up to take in just how big the damn thing was when he noticed the main sail. It was black, with a symbol on it. A star surrounded by what seemed to be flames. The symbol of the Free Will, and the Winchesters themselves. 

"Shit!" He whispered to himself and ducked behind a random house. 

"Find Sam at all costs!" Castiel heard a voice yell as the pirates stormed on land. "whoev'r finds 'im doesn't get a dagger in the chest!" 

"Fuck, I can't get to the Inn now." Castiel felt his chest tighten and began to frantically plan how to get around the pirates in his head. He almost figured it out when one of them turned around the corner where he was hiding. Castiel looked up at the face of a woman.

"Oi, Captain! We got ourselves a little rat." She yelled.

"Wha'dya mean, Ellen?" The voice from earlier asked and swayed over to Castiel and the other pirate. "Well well, yer right. Who are ye?" 

"Castiel" He spoke in hopes of appeasing the pirate in order to keep his life. 

"Well, Casteel. 'ave ye got a surname?" The captain raised his eyebrow. 

"Novak. My name's Castiel Novak." He said. 

"Over here!" Another voice called. "There's still a few pirates over here!"

"Shit, run Ellen. I'll catch up." The captain said. The lady nodded and ran in the opposite direction of the other voices. 

Castiel looked up at the pirate captain and noticed the fear in his eyes. He found himself lost in them and the way the moonlight looked in them. He shook his head and noticed that the pirate drew his sword but faltered once he realized how many soldiers there were. 

"Sorry Sammy." The pirate whispered to himself, silently hoping that Castiel didn't hear. Castiel had mapped out his escape route and decided to save the pirate as well.

"Quickly!" Castiel whispered. "Get in here, I'll distract them." 

The captain looked at Castiel warily. He then looked at the wood shed he was supposed to hide in.

"I'll pass." 

"Trust me." Castiel whispered frantically. "Unless you want to be hanged for your crimes, Winchester." 

The pirate was taken back by Castiel's use of his name. Somehow, the pirate went against everything he ever said and put his trust in a complete stranger. He climbed into the wood shed and sat quietly. Castiel took a shaky breath in and began walking past the next house when he was stopped by the group of soldiers.

"Novak! What are ye doin' 'ere?" The familiar voice called. 

"Gadreel, what 'appened?"Castiel asked, seemingly unaware."

"Pirates, but that isn't import'nt." Gadreel said. "Ye need to get in yer 'ouse."

"I can't, Fin'ly told Naomi to go to 'ell." Castiel said, distracting the soldiers. He hoped.

"Ye 'aven't seen anyone 'round 'ere 'ave ye?" Another soldier said. 

"Nay, no one 'ere but me." Castiel said. 

"Thank ye, Novak." Gadreel said. "C'mon men, they can't 'ave gone far!"

Gadreel gave orders to the rest of the soldiers while he stayed behind. He looked at Castiel with worry written all over his face. He put his hand on Castiel's shoulder.

"Be careful, Castiel. If yer caught with them pirates, they'll 'ave yer head." Gadreel said. "I don't want that fer ye. So tell me, did you see anthin'?"

"I saw nothing, Gadreel." Castiel reiterated. 

Gadreel nodded and ran off to rejoin his squad. Once Castiel was sure Gadreel was gone, he ran back to the wood shed to release the hidden pirate.

"Thank ye." The captain said as he dusted himself off. "I'd be a dead man without ye."

"Yer welcome."

"Why did ye 'elp me?"" The pirate asked. "Ye 'eard the soldier boy. If ye're 'round me ye'll be ex'cuted." 

"Ye looked scared." Castiel said. "And ye apologis'd to Sammy, figur'd he'd want ye alive." 

"I didn't need yer 'elp." The pirate said. "I 'ad it und'r control" 

"Ye jus' said ye'd be dead without me."

"Shut yer mouth."

"'ow 'bout I help ye find yer brother instead?" Castiel said.

"Deal. If ye don't mind nearly dyin' ev'ry oth'r week." 

"What do ye mean?" Castiel furrowed his brows and slightly tilted his head.

"Ye'll 'ave to join me crew." The pirate smiled. "So I can make sure ye don' get yerself kill'd."

"Deal."


	2. Chapter 2

**Summary for the Chapter:**

> Castiel and Captain Winchester of the Free Will find themselves breaking into the prison to rescue the Captain's younger brother.

"Ye'll 'ave to join me crew." The pirate smiled. "So I can make sure ye don' get yerself kill'd."

"Deal." Castiel agreed without hesitation.

"Now, where's me brother?" The captain asked.

"Yer brother's prob'ly bein' 'eld in the prison." Castiel said. "It's near the castle but since the soldiers are busy with yer crew we'll be able to get in easier."

"Okay, take me there." The pirate demanded. "Now."

"Ye can't be serious. I said easier not completly possible. There's still going to be guards who are going to stop at nothing to kill you." Castiel raved. "We need a plan."

"What do ye 'ave in mind?"

"It will be lit'le dang'rous." Castiel smiked sheepishly. "Yer goin' t' get yerself caught."

"I'm sorry?" The captain asked.

"If ye get yerself caught, ye'll be inside of the prison. They'll put ye far away from yer brothers cell t' avoid ye schemin a plan out o' there. I'll climb through the window while ye distract the guards and then I'll get yer brother out. After that I'll call attention to that side of the prison, they'll notice that he's gone and I'll get you out. Then we will all escape."

"And yer sure that it'll work?"

"Yes, I 'ave faith that this will work."

"I be trusting ye Castiel, ye'd better make sure this'll work." The captain spoke harshly. 

"Alright then, let's go." Castiel spoke with slight hesitation. His plan was flawed, he knew that. He knew that the guards might not fall for his trap, but he couldn't let the Winchester know that, he wanted to keep his life. He glanced over at the Winchester and noticed the pained look on his face. He was afraid for his brother, and only wanted him back. 

Castiel looked away quickly once the pirate glanced back at him. The pair weaved quietly through the moon lit streets of Illiac, having only the dim light of the waning moon to see. Castiel, knowing the streets like the backs of his hands, needed nothing to aide him. Forgetting that he was leading another, Castiel kept venturing quickly. Losing the other male in the process.

"Oi, Castiel. I'm no longer behind ye. I cant see where you are or where we be 'eading." The pirate said. 

"Shit, I forgot." Castiel cursed. "I grew up 'ere, ye din't." 

Castiel went back to where he last knew where the pirate was and acknowledged his presence. The pirate shook his head and grunted. 

"We'll never get there in time at this rate." He complained. 

"Damn it." Castiel cursed. He looked at the the pirate and sighed. The man then grabbed hold of the pirate's hand and began to drag him along. However, the pirate shook off the man's grasp. "Look, ye want t' get there quickly and I can get us there but ye need t' put yer big pirate ego aside and be led through these streets by me." 

"I can't." The pirate whispered.

"Do ye want to save yer brother?" 

"I need t' save 'im." The pirate spoke softly in a broken voice. 

"Then take my hand and try to keep up, Winchester." 

"Okay." The pirate whispered and hesitantly slid his hand into the other mans grip. Castiel sighed and began dragging the captain along with him through the streets. Ducking around corners when guards would pass and finally arriving at the prison. 

"We're 'ere, are ye ready Winchester?" Castiel looked over at the pirate.

"As I'll ever be." The captain said and Castiel nodded. 

Castiel began to look around for a way in when he noticed the pirate still held his grip on Castiel's hand. He smiled slightly to himself and decided to hold on just a little longer as well, holding onto the Winchester's hand brought a feeling into his chest that Castiel had never felt before. He could not describe the foreign feeling but he enjoyed it. However, they needed to save Samuel before time ran out. 

"Ye can let go of my 'and now, Winchester." Castiel said after regaining his composure. 

He analyzed the exterior of the prison looking for a point of entry that would keep the two of them out of sight of any guards. Castiel was overjoyed when he noticed an unlatched window almost right next to them. He double and triple checked for any guards when he motioned to the pirate next to him not to follow him through the window and stay hidden. 

Castiel put his hands on the window bottom of the window and hoisted himself up, threw his legs over and, as quietly as he could, he climbed down. Castiel looked around and noticed the rather well kept cells around him were empty.

"Damn it." He cursed softly and turned to the window. 

He leaned out of it to give the pirate outside the signal to get himself caught. Castiel then slipped into the shadow of one of the cells closest to the door. He waited silently as he heard the commotion of the Winchester outside getting himself caught. He listened for the guards coming and capturing the pirate when he thought to himself. 

Why was he helping the pirate? He had originally gotten caught by the pirate and helped because he didn't want to be associated with him. But here he was, helping break the other pirate out of prison. He could walk away from this whole situation. All he'd have to do was double cross the pirate. 

Castiel's thoughts were cut off abruptly just as the guards brought the Winchester through the doors of the prison. He took a deep breath and held it as they crossed the threshold of the room he was in. 

"Put 'im in 'ere, I'd rather 'ave 'im in the dungeon than 'is brother but we can't risk either o' them escaping while bein' mov'd" One of the guards commanded.

"Well well, Winchester. See what 'appens when ye be so careless? Ye get caught and ye'll be 'anged fer yer crimes along with yer brother." One of the guards, who Castiel realized as Ezekiel, laughed.

"We'll see about that." The Winchester spat.

Just as the guard was about to strike the pirate for speaking rudely, Castiel exited his hiding place in the shadows and contemplated leaving or telling the pirate of his betrayal. He smirked and laughed lightly, just enough to catch the attention of the others in the room. 

"You should not have put your trust in some random man you just happened to meet on the street." Castiel said. 

"Novak?" One of the guards asked. "What are ye doin 'ere?"

"Aye, it's me Ezekiel." Castiel said. "I led this pirate here under the false promise of helping rescue his brother."

"Why?" Asked the captain, failing to mask the anger and sadness in his voice.

"You would have either killed me or taken me prisoner if I didn't help you." Castiel spoke. "I had to gain your trust and get rid of you."

The pirate turned away from the bars of his cell and stood seemingly calm. Castiel looked at the guards and said farewell, told the guards not to mention anything that just happened to anyone, and left. As Castiel left, the pirate began to beat on the bars. Screaming curses at Castiel, the pirate promised to kill Castiel for his betrayal. 

Once outside, Castiel took a deep breath and apologized to the Winchester. Saying he needed to make sure the guards knew he wanted nothing to do with the pirate. Still hearing the promises of death from the elder Winchester, Castiel sighed began to monitor his surroundings. Once he was sure he was in the clear, he rushed back into the prison and down to the dungeon where they were holding the younger Winchester. 

As soon as he reached the dungeon, Castiel could immediately tell that these cells were not as well kept as the ones upstairs. He shook his head, hoping to be rid of the foul stench that permeated the air, but to no avail. The elder Winchester could still be heard from even the dungeon, his promises of death still echoing through the underground hallways. He let out a sigh of relief when he located the second Winchester. 

"Samuel Winchester?" Castiel called out softly into the darkness.

"Who are you? What do you want from me?" The Winchester just as quietly.

"My name is Castiel Novak. I'm here to get you out, along with your brother." Castiel whispered as he approached the cell which held the Winchester, examining the lock.

"Then why is my brother promising to kill you?" He seethed quietly.

"I had to convince the guards that I was not helping you at all, removing all suspicion that you two would be leaving tonight. Now enough talking, let's get you out of here." Castiel said and began to pick the lock on the cell. 

As soon as Castiel had the lock undone, he threw it directly into the wall next to the cell and smashed it to pieces. Resulting in aloud sound which would alert the guards. He grabbed the Winchester's arm and ducked into the shadows of the cell across the hall. He motioned for the pirate next to him to be quiet as guards came rushing down the stairs.

The guards turned the corner and noticed that the cell was now empty. Now frightened, they rushed back up the stairs to find the younger Winchester, claiming he couldn't have gotten very far.

As soon as their voices had disappeared into the distance, the pair rushed to the elder Winchester's cell. Castiel, having not spent quite a few hours stuck slumped on the floor of a dungeon, was quicker and reached the captain first. He grabbed onto the lock to pick it when he was grabbed by the throat by the pirate in the prison cell.

"Why are ye 'ere?" The captain seethed. 

"Help.. ing." Castiel choked. 

He was about to lose consciousness when the younger Winchester had finally reached his brother's prison cell to explain to his brother that Castiel was indeed helping. Castiel gathered his breath once again and began picking the lock on the cell once again as the captain apologized. Once the prison cell was open, the brothers were overjoyed and began to have a touching reunion.

"No time, have your reunion later. We need to get out before the guards come back." Castiel urged the brothers. He once again hoisted himself up and out of the window and encouraged the brothers to follow. Once they were out of the prison, Castiel grabbed onto the youngest's wrist and the Captain's hand and began to lead them back to the port. 

The three now fugitives weaved through the frantically searching guards and unlit streets until they reached the port. Their minds all focused on the same thing. Survival. The captain led them aboard the Free Will and gave orders to his brother to release the sails.

"Oi, Novak!" He called to Castiel and tossed a hollowed out animal horn to him. "Blow into that as 'ard as ye can until I tell ye to stop."

Castiel nodded and did as he was told. A sharp, almost painful sound erupting from the hollow horn. He kept on even though he felt as if he were going to pass out. After five long blows, the captain told him to stop and to hang on to the horn. Soon enough the pirate crew began to return to the ship and help get the ship ready to set sail. Castiel watched in amazement as his vision grew dull and blurry. Remembering his name be called by the captain before closing his eyes and falling to the floor of the ship.


	3. Chapter 3

**Summary for the Chapter:**

> Castiel wakes up on the Free Will, confused and slightly in pain. Upon figuring out what happened, Castiel is visited by the Captain in his room and receives his new responsibilities.

Castiel awoke in a pitch black room that seemed to sway gently. He opened his eyes slowly and analyzed the room he was in, it was made of wood and had a curve in the wall. He turned his head slightly and noticed multiple beds all around him. He realized that he was in the infirmary of the Free Will quickly and sighed. He began to sit up but had to stop and lay back town after being prevented by his head hurting so bad he nearly passed out. He pulled the thin blanket back over him and closed his eyes to fall back to sleep when he heard talking between the Winchester brothers.

"You don't have to check on him every hour." Sam said from the hallway outside of the room Castiel was in. 

"Ye don't und'rstan', Sam. There's this feelin in me chest that I can't describe an right now I just need t' talk t' the man in that room." Dean said and opened the door to Castiel's room. 

"Even if he's awake he should rest. Don't you remember what Eileen said?" Sam attempted to reason with his brother as he grabbed his arm, preventing him from walking into the room. "He had too much stress placed on him at once. You need to let him rest before you interrogate him."

"Sammy, if ye don't let me arm go right now, I will 'ave you toss'd in the brig fer mutiny. Do ye und'rstan'?" The elder Winchester fumed.

"Fine." Sam said and forcibly let go of his eldest brother's arm. He stormed off, leaving the captain and Castiel alone. 

By this point Castiel had managed to sit up in his bed and prop himself up against the wall. His head still felt like it was going to explode but he also felt he needed to talk to the Winchester. 

The pirate walked into the room and sighed. He hesitantly wandered over to Castiel's bed but stopped a few feet away when he saw Castiel sitting in his bed.

"Yer awake."

"Ever observant are ye?" Castiel smiled.

"Don't start gettin' snide with me, Castiel." The captain snapped, not maliciously however but more in a friendly manner. 

"just pointin' out the obvious, Winchester." Castiel smiled. "Also, what the 'ell 'appened to me after we got back to the ship?"

"Ye fainted."

"Ye don't say?" Castiel snarked to the captain.

"Eileen says ye 'ad a bit to much excitement an' fainted." The captain said. 

"Eileen?" 

"The onboard doctor." The pirate explained. "She's the best one around."

The captain slowly and rather nervously walked over to Castiel's bed. He stood awkwardly at the foot of it not knowing what else to do. Castiel, not as oblivious as usual then motioned for the pirate to sit at the edge of the bed. He hesitantly took the cue and sat down. He looked at Castiel with a pale face, seemingly nervous. Castiel smiled softly at the flustered Dreaded Captain Winchester that sat gawkily on the edge of his bed. 

"I wan'ed t' apologize fer nearly killin' ye back in the prison." The captain spoke softly. "I was so angry that ye'd trick'd me, I didn't think that ye'd come back. When ye did, I didn't even look at what ye were doin. I jus' react'd."

"It's quite alright, Winchester." Castiel said.

"Dean."

"Sorry?"

"Dean, when talkin' in closed quar'ers ye may call me Dean." The captain said. "it be me name."

"Alright Dean, was there anythin' else ye want'd t' know?"

"What were ye thinkin? Pretendin' to betray me? Ye know who I am and ye know that if ye'd betray'd me I'd stop at nothin' to kill ye. So what the fuck was that?" Dean spoke somewhat angrily. 

"Well, I figured the guards might think ye 'ad someone with ye to get in to the prison. I needed to get all suspicion that ye 'ad 'elp off o' ye so I acted like I'd trick'd ye. I didn't expect ye t' lose yer mind, but ye provided a much needed distraction so I could 'elp yer brother." Castiel explained. 

"I suppose I should thank ye fer savin' me and Sammy. Ye di'n't have t' 'elp 2 strange pirates that ye'd just met." 

"Ye don't 'ave t' thank me, I 'eard ye're leadin the resistance. And if ye are, then I'm 'elping 'cause I 'ate the king just as much as ye." Castiel spoke enthusiastically. 

"That makes me glad. Yer goin' to make a good addition to the crew." Dean smiled.

"Any other questions you have?" 

"A few, actually. Me first is 'ow come ye keep changin' the way ye speak?" 

"Me parents. Me mother, mostly. She 'ad always want'd me to be a scholar and t' study an' find a wife. It was never what I wanted. I hate being in one place for too long. Traveling was always my favorite, ever since I was a wee child." Castiel said. "When you speak like a scholar most people treat you like shit because they want you to know that you aren't better than them. I still switch between them because it's a bad habit."

"I see." Dean nodded and shifted himself more comfortably on Castiel's bed. "Next, why were ye wanderin' that late at night in the first place?"

"Me mother, a wretched beast she is. I finally found some peace while travelin' but she ne'er could just let me be 'appy. I told her how 'orrid she is, to her face while she's in her deathbed in front of all of me siblin's" Castiel laughed lightly. "I couldn't stay there after that so I was on me way t' the inn when ye showed up." 

"Did ye think ye'd be joining a pirate crew when ye left yer father's house last night?" Dean asked.

"I ne'er thought I would e'er be joining a pirate crew t' be completely 'onest, but I think it'll be great. I already travel constantly." 

"Well first things first, what are ye good at? Ye'll need t' be able to pull your own weight with yer chores." Dean asked and stood up from Castiel's bed. "Can ye cook or anythin'?"

"I cannot cook but I can do just about anythin' t' do with carpentry, I am rather skilled with a sword but I don't think that'll help with chores." Castiel said as he slowly climbed out of his bed. 

Dean jumped from his sitting position and went to offer support for Castiel. Castiel denied it however and stood by himself. He stretched his arms over his head and waited until he heard a satisfying pop from his spine. He sat back down, pulled his boots back on and laced them. He looked around him and collected his vest and coat. After buckling his vest he threw his coat back on. He searched around himself again as he searched for his satchel. He noticed it peeking out from under the bed and grabbed it. He threw it over his shoulder and looked at Dean. 

"So what are we doin now?" Castiel asked. 

"I should show ye around the ship a bit." Dean rubbed the back of his neck. "Ye'll be doin carpentry 'round the ship. Fixin' the hull and all of those things." 

"Alright." Castiel nodded and both men meandered out of the room and all over the ship. Castiel followed Dean around as he pointed out every single part of the ship. From the cafeteria, the cargo hold, the brig and the galley, everything there was to see on the Free Will. The pair's last stop was Castiel's new sleeping quarters.

"Ye'll be in 'ere." Dean said as he opened the door to the dusty, obviously vacant room. He gestured for Castiel to enter the room and after Castiel was inside he leaned against the door frame watching as he observed his new room.

Castiel stepped in and looked around. He looked at the cot in the corner and noticed how uncomfortable it seemed. He had no pillow of any sort and had a single spot to hang a lamp next to the cot. There were spider webs in every corner and although Castiel could not see any, he knew that the spiders were there. 

"Ye should 'av told me that I'd 'ave to share with someone else." Castiel smiled at Dean as he gestured to the spiders. 

"Sorry about them, ye're welcome to get rid o' them yerself." Dean smiled right back at Castiel. "They were 'ere first though. Technically the room was theirs first."

"Aye, that be true. I can only 'ope they're willin' to share with me." Castiel smiled. 

"They'll 'ave t' answer t' me about wishin' t' change rooms." Dean smiled.

"Thank ye, Dean." Castiel said and smiled softly. "If ye do not mind I'd like to get just a bit more rest before I start me duties. That be okay with ye?" 

"That will be completely fine. I'll leave ye be."

"Thank ye."

Dean exited the room and Castiel was alone. He sat down abruptly on the edge of the cot and sighed. He placed his head in his head that he propped onto his knees. He had gone abruptly from a traveler who scraped by to a fugitive pirate on the ship belonging to the leaders of the resistance against the king. He needed quite some time to adjust. He had just gotten comfortable on the cot and closed is eyes when he heard a knock on his door.

"Yes?" Castiel called and sat back up as the door opened to reveal a curious looking Sam.

"Hey there, Castiel. How are you settling?"

"I'm fine. As I'll ever be all things considering."

"I can imagine. I just wanted to talk to you for a second." Sam said and closed the door behind him. 

"What's on your mind?" Castiel asked.

"Dean trusts you. He hasn't trusted anyone since our father. If you ever break that trust I will personally kill you." Sam said maliciously. "However, I don't think that'll be the case. You're making him happy, Castiel. I don't know how but you are. For that, I'm glad."

"Make up your mind, Winchester. Do you want to kill me or marry me off to your brother?" Castiel joked in an attempt to cut some of the tension. 

"Either would be fine with me. I don't want to kill you Castiel, but I will if it comes down to it."

"Well then, let's hope it doesn't come down to that." Castiel said defensively. "I only plan on helping Dean take down the king. I have no plans to truly betray him."

"Good. Let' keep it that way." And with that, Sam left. 

Castiel continued staring at the door after Sam left. He tried very hard to make sense of what the hell just happened. After racking his brain for answers to no avail he sighed and flopped back onto his cot. 

"What the hell did just get myself into?" Castiel asked himself. After tossing and turning on the uncomfortable straw mat that was covered by an obviously ratty old piece of cloth, Castiel decided he would not be able to rest and got up to start his newfound responsibilities.

**Notes for the Chapter:**

> Thank you for reading this far! The idea for this story has lived in my brain for quite some time. I just wanted to thank you but I also wanted to apologize for the strange and kind of boring chapter this time. It will get better, I promise!


End file.
